The rights of transgender individuals has been in the headlines during 2017 - ranging from President Trump's tweet to announce a ban on transgender individuals from serving in the military due to the "tremendous medical costs" to a nationwide injunction imposed by a federal district court on the HHS regulations that prohibit health-care discrimination against transgender individuals under the Affordable Care Act (ACA). There are three important reasons why transgender rights are in the news. First, the Human Rights Campaign Foundation, designed to promote the lives of lesbian, gay, bisexual, and transgender (LGBT) people, scores employers in its Corporate Equality Index (CEI) based on their commitment to equal treatment for LGBT employees. To achieve a 100% score in its 2017 CEI, an employer must provide equal health coverage for transgender individuals without exclusion for medically necessary care. This includes medical benefits and services related to transgender transition (e.g., medically necessary services related to sex reassignment). Second, the Seventh Circuit in the summer 2017 decision of Hively v. Ivy Tech Community College held that Title VII's prohibition on sex discrimination in the employment context extends to sexual orientation and gender identity. Third, HHS' regulations prohibiting health-care discrimination against transgender individuals became effective January 1, 2017. As a result of litigation, the portion of those regulations that prohibit discrimination on the basis of gender identity are now subject to a nationwide ban. The Department of Justice's motion requesting a remand and stay of the litigation so that HHS could reconsider its opinion was granted by the federal district court, but the injunction remains in effect. This article discusses the issues facing employers who are considering expansion of their group health plans to include transition-related medical benefits for transgender employees and their beneficiaries for the treatment of gender dysphoria. Issues include federal and state discrimination laws, federal income tax treatment, Title VII prohibitions on sex discrimination in the employment context, and ACA's prohibition against sex discrimination in the health care context. In the backdrop, the Supreme Court has granted cert in the Gloucester County School Bd. v. G.G. case, which will review Title IX's prohibition of sex discrimination in the education context as a school board's policy required students to use the restroom consistent with their birth sex, rather than their gender identity. As the ACA incorporates Title IX's prohibition of sex discrimination into the health care context, the Supreme Court's decision could have far reaching impact.